Adam WeirHomepage Realty
Area guide · Louisville

Douglass Hills, Hurstbourne, Middletown, Anchorage & St. Matthews

A guide to Douglass Hills, Hurstbourne, Middletown, Anchorage, and St. Matthews on the east side of Louisville, covering getting around, shopping, parks, and homes, from a local REALTOR®.

Photo: Unsplash
By the numbers · September 2026
$427,000Median sold price
27Average days on market
107Homes sold
222Homes for sale

Residential properties, September 2026. "For sale" is active listings at month end. Based on information from Metro Search MLS as of October 17, 2026. Deemed reliable but not guaranteed.

Compare every area →

The area at a glance

This part of Louisville covers the east side of the county along Shelbyville Road: Douglass Hills, Hurstbourne, Middletown, the south side of Anchorage, and the east edge of St. Matthews. It runs from around the Watterson Expressway (I-264) out past the Gene Snyder Freeway (I-265), with I-64 along the south. The south end of Lyndon, near Shelbyville Road, falls in this area too. Below is a short section on each one.

Douglass Hills

Where it is

Douglass Hills is its own small city, about 12 miles east of downtown along Shelbyville Road, between Jeffersontown and Middletown. It was farmland from 1813 until the 1970s and became a city in 1973, when the farms were turned into neighborhoods.

Getting around

Shelbyville Road (US 60) runs along the north side. I-64 is about half a mile south, with an exit at Blankenbaker Parkway, so downtown and the rest of the county are an easy drive.

Shopping and food

Shelbyville Road has plenty of shopping and places to eat. Middletown Station, with a Target and a Walmart close by, is a short drive east at Shelbyville Road and North English Station Road.

Parks and outdoors

The city has its own parks, a community swimming pool, and tennis courts. Warren Walker Park has a walking track that is open all year.

The homes

Most homes are single-family houses built in the 1970s and 1980s, when the old farms were split into subdivisions. You will also find some condos, including a few brand-new ones.

Hurstbourne

Where it is

Hurstbourne is its own small city, between Shelbyville Road, Hurstbourne Parkway, I-64, and Oxmoor Center. It takes its name from the Hurstbourne farm, and Lyndon Hall, a house built in the 1840s, is now part of the Hurstbourne Country Club clubhouse.

Getting around

Hurstbourne Parkway runs along the east side and Shelbyville Road along the north. I-64 is right on the south edge, so you can be downtown or out on the Gene Snyder quickly.

Shopping and food

Oxmoor Center sits on the west edge of Hurstbourne. Hurstbourne Parkway near I-64 is lined with shopping centers, restaurants, and office parks.

Parks and outdoors

E.P. “Tom” Sawyer State Park, with trails, a big outdoor pool, and a dog park, is a short drive north. Brown Park in St. Matthews is a few minutes west.

The homes

The neighborhoods sit back from the parkway, away from the offices and shops. Almost all of the land was built out by 1990, so most homes are single-family houses from the 1970s and 1980s.

Middletown

Where it is

Middletown is its own city on the east side of the county along Shelbyville Road. It was set up in 1797 on 500 acres along Beargrass Creek, and the name likely comes from its spot about halfway between Louisville and Shelbyville.

Getting around

Shelbyville Road (US 60) runs through the middle of Middletown. The Gene Snyder Freeway (I-265) has an exit at Shelbyville Road, and I-64 runs just to the south.

Shopping and food

Middletown Commons, on Shelbyville Road just east of town, has stores like Hobby Lobby and Ross plus restaurants. Middletown Station at North English Station Road has more shops, with a Target and a Walmart close by. Main Street in the old part of town has a few local shops.

Parks and outdoors

Beckley Creek Park, at Shelbyville Road, is the north end of The Parklands of Floyds Fork, a 4,000-acre park system that runs about 20 miles. It has a big open lawn with a walking loop and miles of trails.

The homes

Most homes are single-family houses, with neighborhoods built in every decade from the 1950s to the 2000s. You will also find townhomes and condos.

Anchorage

Where it is

Anchorage is its own small city, about 15 miles east of downtown. It became a city in 1878 and is named after The Anchorage, the estate of a riverboat captain. Anchorage is split between two MLS areas, and this one covers its south side, around Evergreen Road. The north side is in the area with Glenview, Lyndon, and Prospect.

Getting around

Evergreen Road runs north and south through this side of Anchorage, and Shelbyville Road is just to the south. The Gene Snyder Freeway (I-265) has exits at Old Henry Road and La Grange Road.

Shopping and food

Anchorage itself is almost all homes. For shopping and restaurants, Shelbyville Road and Middletown are just a few minutes south.

Parks and outdoors

The Anchorage Trail is a 2.1-mile walking trail that opened in 2008. Beckley Creek Park is a short drive east.

The homes

Homes on this side of Anchorage sit on wooded lots, some close to an acre, many built in the 1950s and 1960s. You will also find newer subdivisions from the 1990s and 2000s nearby.

St. Matthews

Where it is

St. Matthews is its own city, about 7 miles east of downtown, and it was once one of the biggest potato-growing areas in the country. St. Matthews is split between two MLS areas. Most of it is in the area with Clifton and Crescent Hill, and this one covers a small piece of its east side, around Warwick Village.

Getting around

Shelbyville Road (US 60) and Westport Road are the main roads, and the Watterson Expressway (I-264) is just to the west, so downtown and the rest of the county are an easy drive.

Shopping and food

Oxmoor Center and Mall St. Matthews are both close by, and Shelbyville Road is lined with smaller shopping centers and restaurants.

Parks and outdoors

Warwick Park is right in the neighborhood, with a pavilion, basketball goals, a playground, and a walking track. Brown Park, with trails along Beargrass Creek, is a short drive west.

The homes

Most homes around Warwick Village are single-family houses from the 1950s and 1960s. A few new homes and townhomes have gone up here in the last few years.

Thinking about this part of town?

I am happy to show you around or answer any questions about the area. Let’s talk.

← All areas